Most retirement advice focuses on money — how much you need, how to invest it, and whether you’ll run out. But here’s the thing: money alone doesn’t create a happy retirement.
I’ve worked with retirees who have millions and still feel lost, and others with modest savings live incredibly fulfilling lives. After building many retirement plans for those entering their golden years, I’ve learned that these seven questions matter just as much as the size of your portfolio. And once you understand them, retirement begins to look completely different.
Are you planning for healthspan, not just lifespan?
One of the best books I’ve ever read is Outlive: The Science and Art of Longevity by Dr. Peter Attia. In it, he makes a powerful distinction between lifespan — how long you live — and healthspan — how long you live well.
Attia’s core message is that modern medicine has done a great job of helping people live longer, but not necessarily better. Many of us spend the final decade or two of our lives in poor health, unable to enjoy the wealth and freedom we worked so hard for.
He talks about “playing the long game” with your body — building strength, endurance, and metabolic health early, so you can keep doing the things you love in your 60s, 70s, and beyond. It’s not about chasing youth forever, but extending the years you can live fully and independently.
If you’re nearing retirement, this is worth reflecting on. There’s little point in delaying retirement if your best years — your healthiest years — are slipping away. I highly recommend reading Outlive for anyone who’s planning their next chapter in life. It’s a reminder that the goal isn’t just to live longer, but to live better for as long as you can.
Have you maxed out your fulfillment at work?
If you hate your job, dread your coworkers, or feel like you’ve already accomplished all your work goals and are just counting the days until you retire, you probably already know the answer — it might be time to move on. Work is supposed to challenge and energize you, not drain you.
But if you genuinely love what you do, find purpose in it, and it gives your life meaning, maybe you’ll never want to stop. Retirement isn’t a finish line for everyone. For some, it’s just the freedom to keep doing what they love without pressure.
A great example is Warren Buffett, one of the richest men on earth. At 94 years old, after more than six decades at the helm of Berkshire Hathaway, he finally announced that he’ll step down as CEO at the end of 2025. This was a man who obviously didn’t need the money, but he truly enjoyed and loved his work.
But most of us aren’t Warren Buffett. For most people, there comes a point where the emotional and mental return on work starts to fade, even if the paycheck doesn’t. The real question is: does your work still fill you up — or is it quietly emptying your time and energy?
Are you prepared for the ‘honeymoon phase’ of retirement?
The honeymoon phase of retirement is often overlooked — but it can be one of the most dangerous parts of the transition. At first, everything feels exciting. No deadlines, no meetings, no alarm clocks. It’s a rush of freedom that can last a few months or even a few years.
But what many people don’t realize is that this phase will fade, just like every other honeymoon phase of life that you’ve experienced such as marriage, or starting a new career, etc.
When the novelty wears off, it can leave a sense of emptiness or even depression if there isn’t something meaningful to replace the structure that work once provided. It’s an understated risk that catches a lot of new retirees off guard.
Retirement is like flying on a plane. Takeoff can be exciting, but you need a plan for fuel, turbulence, and a smooth landing.
That’s why it’s important to think beyond the initial excitement. The retirees who thrive long-term are the ones who plan for what comes after the honeymoon, which brings me to my next point…
Do you have a clear purpose and vision for retirement?
Retirement isn’t just about leaving work — it’s about moving toward something that gives your life meaning. The happiest retirees aren’t the ones with the biggest portfolios, but the ones who wake up with a reason to get out of bed. Maybe it’s traveling more, spending time with family, exploring your creative side, volunteering, or finally chasing the goals you put off during your career.
Without a sense of purpose, retirement can quickly lose its shine. The first few months might feel like a long vacation, but without direction, boredom and restlessness start to creep in. That’s why it’s important to think about not just what you’re retiring from, but what you’re retiring to.
A clear vision gives structure to your days, meaning to your time, and energy to your years ahead. So ask yourself — what are you most excited to do once work is no longer the center of your life?
If you want a retirement plan that shows how long your money will last and how to protect it from taxes and market drops, that’s what we do at Blueprint Financial. Build the life you want, with the right Blueprint. Visit our website and book a discovery call.
Do you have clear financial goals for retirement?
You’ve decided what money is really for. Maybe your goal is to enjoy life fully and die with zero — a concept popularized by Bill Perkins in his book of the same name, where the aim is to spend your wealth on meaningful experiences while you’re still healthy enough to enjoy them.
Or perhaps you want to leave a meaningful legacy for your loved ones or a charity, or even build generational wealth that supports your family for lifetimes to come.
There’s no right or wrong answer — what matters is that you’ve thought it through. When your financial goals align with your personal values, every spending, saving, and investing decision becomes easier. So ask yourself, how will you use your money intentionally to live the kind of life — and leave the kind of impact — that matters most to you.
Do you have enough to retire?
Everyone wants to know the million-dollar question — do I have enough to retire? But enough isn’t a number on a screen. It’s how your entire financial picture — your spending, income, taxes, and investments — all connect to support the life you actually want. This is the question we help our clients with the most, and it can get quite technical.
Before you can retire confidently, you need to understand how these pieces connect.
1. Expenses
Start by getting clear on how much your lifestyle actually costs. Track what you spend — not just on essentials like groceries and utilities, but also on travel, hobbies, and healthcare. It’s easy to underestimate. And remember that your spending won’t stay constant over time. Many retirees go through three phases: the “go-go years” early on, when travel and leisure spending peak; the “slow-go years,” when spending naturally dips; and the “no-go years,” when health-related costs rise again.
Meet Glenn, 65. He wants to plan out his retirement, and came to us here at Blueprint to build him a financial plan. He calculated that he needs about $65,000 a year after tax to live comfortably. That includes golf, dinners out, and a few small trips. Glenn expects higher spending early in retirement, tapering in his 70s, and he’s built those shifts into his plan, plus we planned for inflation.
2. Income Sources
Once you know what you’ll spend, you need to figure out where that money will come from — CPP, OAS, pensions, RRSPs, TFSAs, or non-registered accounts. The challenge isn’t just accumulating assets, but managing the timing of withdrawals. The right strategy can stretch your money much further.
Glenn has about $950,000 saved across his RRSP, TFSA, and a non-registered account. His plan is to draw from his RRSP first and delay CPP and OAS until age 70. At that time he’ll receive $25,000 a year in CPP and OAS. That gives him higher guaranteed income later and reduces the pressure on his investments during downturns. His TFSA provides tax-free flexibility to fill income gaps or fund special goals.
3. Investments
Your portfolio has to match your comfort with risk and your spending needs in retirement. Too much risk can lead to sleepless nights — too little can leave you short of growth. For most people, a balanced, diversified portfolio lets your money grow while protecting what you’ve built, but it depends on your specific risk tolerance.
Glenn’s investments are 60% in diversified equities and 40% in bonds and cash. This mix gives him enough growth to keep up with inflation, while still holding a few years of expenses in stable assets. He rebalances annually and adjusts his portfolio as markets and life change.
4. Tax Planning
Taxes don’t disappear in retirement — they just change shape. Every dollar you withdraw from your RRSP or RRIF is fully taxable, and if your income climbs too high, you could lose part of your OAS to clawback. The order and timing of withdrawals make a big difference.
Glenn’s planner helped him map out a tax-efficient withdrawal plan: modest RRSP withdrawals in his mid 60s, topping up income from his TFSA when needed, and leaving his non-registered account for later flexibility. This keeps his taxable income stable and helps him avoid unnecessary clawbacks. End result – his money is projected to last until the ripe age of 97.
Have You Planned for the Unexpected?
Even the best retirement plan can fall apart if it only works when everything goes right. Life doesn’t follow a straight line — markets dip, inflation spikes, health issues arise, or a family member might need help. The question isn’t if surprises will happen, but whether your plan can handle them.
Planning for the unexpected means stress-testing your finances against real-world scenarios. What happens if investment returns are lower than expected for a few years? If inflation runs higher than normal? Or if you live 10 years longer than you planned? The goal isn’t to predict the future — it’s to make sure your plan is flexible enough to adapt.
Take Glenn, for example. His original retirement plan showed he could retire at 65 and his money would comfortably last to age 97. But when we stress-tested his plan — using randomized returns and higher inflation assumptions — the story changed.
In the “bad” scenario, where his investments only earn around 2% per year and inflation stays elevated, his savings run out at age 88.
At this point, it becomes a question of how much certainty you want to build into your plan, and what adjustments you’re willing to make to get there — spending slightly less, working a bit longer, earning more, or adjusting the investment mix.
Glenn is comfortable with the base scenario that takes him to age 97, but after seeing how his more aggressive investments might shorten the life of his portfolio, he’s decided to dial things back. By shifting to a slightly more conservative mix, he reduces the chances of a major market downturn derailing his retirement.
If Glenn had come to us a few years earlier, he might have had the peace of mind to retire a couple of years sooner.
Retirement isn’t just about stopping work — it’s about designing a life you can enjoy for decades, with health, purpose, and confidence. If you want a personalized retirement plan that shows how long your money will last and what steps you should take now, our team can help.
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